Water → HCID 70819417, compound

HRID 591028Notes

Reaction equation

HRID 591028 reaction equation
[Br:1]N1C(=O)CCC1=O.N(C1(C#N)CCCCC1)=NC1(C#N)CCCCC1.[O:27]1[C:31]2[CH:32]=[CH:33][CH:34]=[CH:35][C:30]=2[C:29]([CH:36]([O:42][C:43]([CH3:46])([CH3:45])[CH3:44])[C:37]([O:39][CH2:40][CH3:41])=[O:38])=[CH:28]1.O>C(Cl)(Cl)Cl>[Br:1][C:28]1[O:27][C:31]2[CH:32]=[CH:33][CH:34]=[CH:35][C:30]=2[C:29]=1[CH:36]([O:42][C:43]([CH3:45])([CH3:44])[CH3:46])[C:37]([O:39][CH2:40][CH3:41])=[O:38]

Participants

6

Reactant 4

HCID 962WaterHCID 67184N-bromobutanimideHCID 749781,1'-Azobis(cyclohexanecarbonitrile)HCID 70819504HCID 70819504, compound

Product 1

HCID 70819417HCID 70819417, compoundYield 46%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

N-Bromosuccinimide (265 mg, 1.48 mmol) and 1,1′-Azobis(cyanocyclohexane) (20 mg, 0.06 mmol) were added to a solution of ethyl 2-(1-benzofuran-3-yl)-2-(tert-butoxy)acetate (20b) (340 mg, 1.23 mmol) in chloroform (5 mL). The reaction mixture was refluxed for 5 hours. Water (5 mL) was added and the mixture was extracted with ethyl acetate (2×10 mL). The organic layer was dried over sodium sulfate and evaporated to dryness. The residue was purified by flash chromatography on silica gel (cyclohexane/ethyl acetate: 95/05) to provide ethyl 2-(2-bromo-1-benzofuran-3-yl)-2-(tert-butoxy)acetate (20c) (200 mg, 0.56 mmol, 46%).

Workup

  1. temperatureThe reaction mixture was refluxed for 5 hours
  2. extractionthe mixture was extracted with ethyl acetate (2×10 mL)
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. customevaporated to dryness
  5. customThe residue was purified by flash chromatography on silica gel (cyclohexane/ethyl acetate: 95/05)

Sources & evidence

ORD record
ord-cdb2eaf2984d45deab99120c380ac35a
Source dataset
uspto-grants-2016_01
Patent number
US09238026B2

Reaction notes

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